Open Access Open Access  Restricted Access Subscription Access

NEW APPROACH TO THE SYNTHESIS OF 2,2':5',2''-TERTHIOPHENE-5,5''- AND 2,2':5',2'':5'',2'''-QUATERTHIOPHENE-5,5'''-DICARBOXYLIC ACIDS

Анастасия С. Костюченко, Евгений Б. Ульянкин, Антон Л. Шацаускас, Владислав Ю. Шувалов, Александр С. Фисюк
Cover Image

Abstract


The reaction of bromosuccinimide with esters of 3-substituted 2,2'-bithiophene-5-carboxylic acids was used to obtain their 5'-bromo derivatives, which were further converted to esters of 3,3'''-disubstituted 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids by heating in DMF with catalytic amounts of Pd(PPh3)4. Ester of 3-decyl-2,2'-bithiophene-5-carboxylic acid was acylated at the С-5' position with lauroyl chloride in the presence of SnCl4, producing the respective ketone that was used in Vilsmeier–Haack reaction (DMF, POCl3). The 3-chloroacrylaldehyde derivative that was thus obtained was further used in reaction with ethyl thioglycolate in the presence of sodium ethoxide, giving ester of 3,3''-decyl-2,2':5',2''-terthiophene-5,5''-dicarboxylic acid. Alkaline hydrolysis of the obtained esters led to the corresponding 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''- and 2,2':5',2''-terthiophene-5,5''-dicarboxylic acids.

Authors: Anastasia S. Kostyuchenko, Evgeny B. Ulyankin, Anton L. Shatsauskas, Vladislav Yu. Shuvalov, Alexander S. Fisyuk*


Keywords


2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids; 2,2':5',2''-terthiophene-5,5''-dicarboxylic acids; esters of 3-alkyl- 2,2'-bithiophene-5-carboxylic acids

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv